Great Question is the all-in-one AI customer research platform for understanding your customers. Backed by world-class investors and trusted by industry-leading teams like Gusto, Experian, Canva, and Brex, we’re building the future of customer research.

We believe AI is a multiplier for creativity, speed, and scale. Everyone on the team is encouraged to lean into AI, not just to be more efficient, but to push boundaries and unlock new possibilities. Whether you’re writing, designing, coding, or analyzing, we expect you to explore how AI can elevate your craft.

Our culture is built on high trust, high agency, and high emotional intelligence.

Product

Engineer (Full-Stack) - Canada, Remote My co-founder Ned and I built this company on a simple idea: talking to your customers should be easy. Research, design, and product teams at ServiceNow, Brex and Canva run their customer research on us, and we raised a $13M Series A led by Inovia late last year after going through YC in 2021.

We’re super excited about what we’ve built and now we need help to continue rebuilding core parts of our product, agent‑first. I’m hiring our first Product Engineers in Canada to do it with us.

Product Engineer here means you take a problem and run with it end to end - from the customer conversation to production to validating whether it actually worked. PM support is light and as‑required: a PM helps size the problem, shape the appetite, and call priority, but nobody hands you a spec. From there you're trusted to find the right solution, because you're close to the customer and you have great product sense.

You’ll build across the product stack - from Rails APIs and React/TypeScript frontends to video streaming, realtime voice agents, agentic search, product analytics, and everything in between - working directly with the founders, our designer, and the rest of engineering.

AI is embedded across your entire workflow - not just used for coding. You might spend a morning digging through interview transcripts and product analytics to understand a problem, build a few throwaway prototypes to see which approach holds up,



and then build a technical plan before handing it to a couple of agents to build and QA.

We’re expecting great judgment around all of that: breaking work into sensible pieces, evaluating the output carefully, and most importantly, owning whatever ships, regardless of who typed it.

You build highly usable, customer‑centric products that people love. You take the extra time to really dig into the data to make sure you understand the problem; You’ll go the extra mile to deliver something with UI + UX polish, while also thinking in systems to make sure that you’re using the right primitives so you’re delivering less bespoke solutions.

We're a small team of exceptional engineers, and we only hire people who raise the bar.

An expert in both exposing APIs and the frontend it sits upon. We’re a Rails and TypeScript team, but it’s not a hard requirement. Shipping features live and then maintaining them long enough to see what works (and what doesn’t!) Live in an agentic coding harness daily (Claude Code, Codex, Cursor - we don't care which) and have real opinions about your setup.

Ideally shipped LLM-powered features, or least know what it takes to run them in production. Have shipped things where you decided what to build, and can defend your UX opinions. We're remote and async-heavy; Are senior (roughly 5+ years with real ownership).

We've rebuilt how we work around AI agents, to ensure our engineers are unblocked to work at AI native speeds:

Main goes to production and approvals aren’t always required.

We invest in making the codebase easy to work in: written runbooks and conventions that help agents and new people find their way around quickly. This might not be for everyone, but if it excites you, we’re especially keen to meet people who are willing to challenge some of these ideas with their own hard-won lessons from the arena.





You’re deep in the customer data, in their Slack channels, and solving problems. ship into a live area. That might be AI Moderator quality, or working directly on our global chat experience. you're deep on a product area: talking to its customers, deciding what's next, accountable for whether it worked. Ambiguity and shifting priorities wear you down.

We’re a small team, remote, and with light processes… resourcefulness is critical to the job. You’re not all‑in on AI. Dabbling won't cut it here. You’d rather not talk to customers. Product engineers here get on calls, read transcripts, and sit in the support queue sometimes.

Plenty of weeks are polish, reliability, and making something 5% less annoying. You want a PM to frame the problem and hand you a spec. “Full-time employment with proper benefits, generous salary in CAD. Remote, anywhere in Canada.

We generally work PST hours, but are adaptable. Our offers sit in a defined band for the level, and set by our internal leveling rubric (scope of ownership, technical depth, previous relevant experience), not by negotiation. Your story, what you've shipped.

Quality session (~ 60 min). Do you know what quality looks like - both in terms of product and code. Building session (~90 min) . Build something real in our domain with your own AI tooling, the way you actually work; We reimburse AI credits.

AI tools aren't just allowed - they're expected just as they are in the job.

A culture of customer obsession and curiosity Remote-first culture with high trust and high autonomy Annual team retreats and virtual events Opportunity to work on cutting‑edge AI integrations that matter Competitive compensation & equity We expect every member of the Great Question community to do their part to cultivate and maintain an environment where everyone has the opportunity to feel included, and is afforded the respect and dignity they deserve.

Decisions related to hiring, compensating, training, evaluating performance, or terminating are made fairly, and we provide equal employment opportunities to all qualified candidates and employees.

📌 Product Engineer (AI / Full-Stack) at Great Question (Winnipeg)
🏢 Matcha
📍 Winnipeg